IE49046B1 - Carbamoyloxy penicillin and cephalosporin derivatives and the production of 3-cephems - Google Patents
Carbamoyloxy penicillin and cephalosporin derivatives and the production of 3-cephemsInfo
- Publication number
- IE49046B1 IE49046B1 IE947/79A IE94779A IE49046B1 IE 49046 B1 IE49046 B1 IE 49046B1 IE 947/79 A IE947/79 A IE 947/79A IE 94779 A IE94779 A IE 94779A IE 49046 B1 IE49046 B1 IE 49046B1
- Authority
- IE
- Ireland
- Prior art keywords
- group
- isocyanate
- compound
- substituted
- hydrogen
- Prior art date
Links
- -1 Carbamoyloxy penicillin Chemical class 0.000 title claims abstract description 331
- 229930182555 Penicillin Natural products 0.000 title description 11
- 229940049954 penicillin Drugs 0.000 title description 9
- 229930186147 Cephalosporin Chemical class 0.000 title description 5
- 229940124587 cephalosporin Drugs 0.000 title description 5
- 150000001780 cephalosporins Chemical class 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 91
- 239000012948 isocyanate Substances 0.000 claims abstract description 66
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 58
- 238000000034 method Methods 0.000 claims description 101
- 229910052739 hydrogen Inorganic materials 0.000 claims description 68
- 239000001257 hydrogen Substances 0.000 claims description 68
- 125000000217 alkyl group Chemical group 0.000 claims description 60
- 125000003118 aryl group Chemical group 0.000 claims description 55
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 54
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 50
- 125000002252 acyl group Chemical group 0.000 claims description 36
- 125000003545 alkoxy group Chemical group 0.000 claims description 36
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 34
- 125000004414 alkyl thio group Chemical group 0.000 claims description 33
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 23
- 229910052751 metal Inorganic materials 0.000 claims description 21
- 239000002184 metal Substances 0.000 claims description 21
- 229910052755 nonmetal Inorganic materials 0.000 claims description 21
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 150000002843 nonmetals Chemical group 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 150000002148 esters Chemical class 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 125000004104 aryloxy group Chemical group 0.000 claims description 16
- 239000003960 organic solvent Substances 0.000 claims description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 13
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- OCKPROYBCPQWJO-UHFFFAOYSA-N acetyl isocyanate Chemical compound CC(=O)N=C=O OCKPROYBCPQWJO-UHFFFAOYSA-N 0.000 claims description 11
- GRNOZCCBOFGDCL-UHFFFAOYSA-N 2,2,2-trichloroacetyl isocyanate Chemical compound ClC(Cl)(Cl)C(=O)N=C=O GRNOZCCBOFGDCL-UHFFFAOYSA-N 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 230000002140 halogenating effect Effects 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 239000011593 sulfur Substances 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 8
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 7
- 239000011230 binding agent Substances 0.000 claims description 7
- OUPLTJDZPQZRBW-UHFFFAOYSA-N n-(oxomethylidene)methanesulfonamide Chemical group CS(=O)(=O)N=C=O OUPLTJDZPQZRBW-UHFFFAOYSA-N 0.000 claims description 7
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 7
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 7
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical compound O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 claims description 7
- 125000003441 thioacyl group Chemical group 0.000 claims description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 6
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- YOVQDZPAVARTTR-UHFFFAOYSA-N methyl n-(oxomethylidene)carbamate Chemical compound COC(=O)N=C=O YOVQDZPAVARTTR-UHFFFAOYSA-N 0.000 claims description 5
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims description 5
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 4
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 4
- 239000002552 dosage form Substances 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 4
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 4
- 125000005544 phthalimido group Chemical group 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 4
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- YNKDRTCJDFVUTJ-UHFFFAOYSA-N carbonyl diisocyanate Chemical compound O=C=NC(=O)N=C=O YNKDRTCJDFVUTJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 150000007529 inorganic bases Chemical class 0.000 claims description 3
- BUZRAOJSFRKWPD-UHFFFAOYSA-N isocyanatosilane Chemical compound [SiH3]N=C=O BUZRAOJSFRKWPD-UHFFFAOYSA-N 0.000 claims description 3
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 3
- CMNXBYHSNBLXDN-UHFFFAOYSA-N (4-nitrophenyl)methyl n-(oxomethylidene)carbamate Chemical compound [O-][N+](=O)C1=CC=C(COC(=O)N=C=O)C=C1 CMNXBYHSNBLXDN-UHFFFAOYSA-N 0.000 claims description 2
- UBCNWGMGMVGVIJ-UHFFFAOYSA-N 1-chloro-n-(oxomethylidene)methanesulfonamide Chemical compound ClCS(=O)(=O)N=C=O UBCNWGMGMVGVIJ-UHFFFAOYSA-N 0.000 claims description 2
- UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 claims description 2
- 125000005808 2,4,6-trimethoxyphenyl group Chemical group [H][#6]-1=[#6](-[#8]C([H])([H])[H])-[#6](-*)=[#6](-[#8]C([H])([H])[H])-[#6]([H])=[#6]-1-[#8]C([H])([H])[H] 0.000 claims description 2
- BIGWKPQWUGNMSE-UHFFFAOYSA-N 2,4-dinitro-n-(oxomethylidene)benzenesulfonamide Chemical compound [O-][N+](=O)C1=CC=C(S(=O)(=O)N=C=O)C([N+]([O-])=O)=C1 BIGWKPQWUGNMSE-UHFFFAOYSA-N 0.000 claims description 2
- RRXCOMRSZAQORJ-UHFFFAOYSA-N 2,4-dinitrobenzoyl isocyanate Chemical compound [O-][N+](=O)C1=CC=C(C(=O)N=C=O)C([N+]([O-])=O)=C1 RRXCOMRSZAQORJ-UHFFFAOYSA-N 0.000 claims description 2
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
- PRMQJMFYVGKRGH-UHFFFAOYSA-N 2-cyanoacetyl isocyanate Chemical compound O=C=NC(=O)CC#N PRMQJMFYVGKRGH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
- HEBTZZBBPUFAFE-UHFFFAOYSA-N 2-methyl-n-(oxomethylidene)benzenesulfonamide Chemical compound CC1=CC=CC=C1S(=O)(=O)N=C=O HEBTZZBBPUFAFE-UHFFFAOYSA-N 0.000 claims description 2
- SMTUNIMBRXGDKX-UHFFFAOYSA-N 2-phenylacetyl isocyanate Chemical compound O=C=NC(=O)CC1=CC=CC=C1 SMTUNIMBRXGDKX-UHFFFAOYSA-N 0.000 claims description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000006279 3-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Br)=C1[H])C([H])([H])* 0.000 claims description 2
- BXLRBPNDOBBLHO-UHFFFAOYSA-N 4-nitro-n-(oxomethylidene)benzenesulfonamide Chemical compound [O-][N+](=O)C1=CC=C(S(=O)(=O)N=C=O)C=C1 BXLRBPNDOBBLHO-UHFFFAOYSA-N 0.000 claims description 2
- DRCVWVLUBDJADC-UHFFFAOYSA-N 4-nitrobenzoyl isocyanate Chemical compound [O-][N+](=O)C1=CC=C(C(=O)N=C=O)C=C1 DRCVWVLUBDJADC-UHFFFAOYSA-N 0.000 claims description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
- LURYMYITPCOQAU-UHFFFAOYSA-N benzoyl isocyanate Chemical compound O=C=NC(=O)C1=CC=CC=C1 LURYMYITPCOQAU-UHFFFAOYSA-N 0.000 claims description 2
- DPLPYEOVMXECQX-UHFFFAOYSA-N benzyl n-(oxomethylidene)carbamate Chemical compound O=C=NC(=O)OCC1=CC=CC=C1 DPLPYEOVMXECQX-UHFFFAOYSA-N 0.000 claims description 2
- VKYUIYJITRRKMZ-UHFFFAOYSA-N benzyl n-(oxomethylidene)sulfamate Chemical compound O=C=NS(=O)(=O)OCC1=CC=CC=C1 VKYUIYJITRRKMZ-UHFFFAOYSA-N 0.000 claims description 2
- OBMGCMDXJDMDQU-UHFFFAOYSA-N butanoyl isocyanate Chemical class CCCC(=O)N=C=O OBMGCMDXJDMDQU-UHFFFAOYSA-N 0.000 claims description 2
- HNMKOFNBCMOOQW-UHFFFAOYSA-N cyanoformyl isocyanate Chemical compound O=C=NC(=O)C#N HNMKOFNBCMOOQW-UHFFFAOYSA-N 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- PGJJYYADLKWXLJ-UHFFFAOYSA-N isocyanato(trimethoxy)silane Chemical compound CO[Si](OC)(OC)N=C=O PGJJYYADLKWXLJ-UHFFFAOYSA-N 0.000 claims description 2
- NIZHERJWXFHGGU-UHFFFAOYSA-N isocyanato(trimethyl)silane Chemical group C[Si](C)(C)N=C=O NIZHERJWXFHGGU-UHFFFAOYSA-N 0.000 claims description 2
- JNFUJVWWFWBAFI-UHFFFAOYSA-N isocyanato(triphenyl)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(N=C=O)C1=CC=CC=C1 JNFUJVWWFWBAFI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical compound O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 claims description 2
- FADNAWIZFDFJSH-UHFFFAOYSA-N n-(oxomethylidene)ethanesulfonothioamide Chemical compound CCS(=O)(=S)N=C=O FADNAWIZFDFJSH-UHFFFAOYSA-N 0.000 claims description 2
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- BFKZWJPWBGAKLZ-UHFFFAOYSA-N phenyl n-(oxomethylidene)sulfamate Chemical compound O=C=NS(=O)(=O)OC1=CC=CC=C1 BFKZWJPWBGAKLZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000003333 secondary alcohols Chemical class 0.000 claims description 2
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 2
- LLROOTQECVJATI-UHFFFAOYSA-N triethoxy(isocyanato)silane Chemical compound CCO[Si](OCC)(OCC)N=C=O LLROOTQECVJATI-UHFFFAOYSA-N 0.000 claims description 2
- VIGRJDWPNTXJSQ-UHFFFAOYSA-N triethyl(isocyanato)silane Chemical compound CC[Si](CC)(CC)N=C=O VIGRJDWPNTXJSQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 9
- 238000007796 conventional method Methods 0.000 claims 5
- 125000001931 aliphatic group Chemical group 0.000 claims 3
- 150000001734 carboxylic acid salts Chemical class 0.000 claims 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 1
- JDRFUUBRGGDEIZ-UHFFFAOYSA-N 3,6-dichloro-2-methoxybenzoate;dimethylazanium Chemical compound CNC.COC1=C(Cl)C=CC(Cl)=C1C(O)=O JDRFUUBRGGDEIZ-UHFFFAOYSA-N 0.000 claims 1
- 101100496114 Caenorhabditis elegans clc-2 gene Proteins 0.000 claims 1
- 206010007134 Candida infections Diseases 0.000 claims 1
- 101150065749 Churc1 gene Proteins 0.000 claims 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 1
- 102100038239 Protein Churchill Human genes 0.000 claims 1
- DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 claims 1
- 125000003172 aldehyde group Chemical group 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 claims 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
- 125000000075 primary alcohol group Chemical group 0.000 claims 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004149 thio group Chemical group *S* 0.000 claims 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 claims 1
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 claims 1
- 150000001782 cephems Chemical class 0.000 abstract description 31
- FCZNNHHXCFARDY-WQRUCBPWSA-N (2s,5r,6r)-3,3-dimethyl-4,7-dioxo-6-[(2-phenylacetyl)amino]-4$l^{4}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical class N([C@H]1[C@@H]2N(C1=O)[C@H](C(S2=O)(C)C)C(O)=O)C(=O)CC1=CC=CC=C1 FCZNNHHXCFARDY-WQRUCBPWSA-N 0.000 abstract description 16
- 125000001424 substituent group Chemical group 0.000 abstract description 14
- 150000001781 cephams Chemical class 0.000 abstract description 12
- 150000002959 penams Chemical class 0.000 abstract description 9
- LFMBIMXJWIQULB-SSDOTTSWSA-N (6r)-3-methyl-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical compound S1CC(C)=CN2C(=O)C[C@H]21 LFMBIMXJWIQULB-SSDOTTSWSA-N 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 102
- QHTOIDKCEPKVCM-ZCFIWIBFSA-N cepham Chemical compound S1CCCN2C(=O)C[C@H]21 QHTOIDKCEPKVCM-ZCFIWIBFSA-N 0.000 description 49
- WSHJJCPTKWSMRR-RXMQYKEDSA-N penam Chemical compound S1CCN2C(=O)C[C@H]21 WSHJJCPTKWSMRR-RXMQYKEDSA-N 0.000 description 46
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 239000000047 product Substances 0.000 description 40
- 239000000243 solution Substances 0.000 description 39
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
- 229910001868 water Inorganic materials 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 29
- 239000006260 foam Substances 0.000 description 25
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 24
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- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- AIFMYMZGQVTROK-UHFFFAOYSA-N silicon tetrabromide Chemical compound Br[Si](Br)(Br)Br AIFMYMZGQVTROK-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical group O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- LTSUHJWLSNQKIP-UHFFFAOYSA-J tin(iv) bromide Chemical compound Br[Sn](Br)(Br)Br LTSUHJWLSNQKIP-UHFFFAOYSA-J 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- GEWRGPBMDJVIDP-UHFFFAOYSA-N trichloro(isocyanatosulfanyl)methane Chemical compound ClC(Cl)(Cl)SN=C=O GEWRGPBMDJVIDP-UHFFFAOYSA-N 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- 125000006000 trichloroethyl group Chemical group 0.000 description 1
- QRTBHOAAJDKKOU-UHFFFAOYSA-N trifluoro(isocyanatoselanyl)methane Chemical compound FC(F)(F)[Se]N=C=O QRTBHOAAJDKKOU-UHFFFAOYSA-N 0.000 description 1
- OZEFVOPTJSERLH-UHFFFAOYSA-N trifluoro(isocyanatosulfanyl)methane Chemical compound FC(F)(F)SN=C=O OZEFVOPTJSERLH-UHFFFAOYSA-N 0.000 description 1
- AUILUEXXDWUIBU-UHFFFAOYSA-N triisocyanatoalumane Chemical compound [Al+3].[N-]=C=O.[N-]=C=O.[N-]=C=O AUILUEXXDWUIBU-UHFFFAOYSA-N 0.000 description 1
- SZXLFRCOEKCGSL-UHFFFAOYSA-N triisocyanatoborane Chemical compound O=C=NB(N=C=O)N=C=O SZXLFRCOEKCGSL-UHFFFAOYSA-N 0.000 description 1
- QLYZQYBAIRVLPF-UHFFFAOYSA-N triisocyanatostibane Chemical compound O=C=N[Sb](N=C=O)N=C=O QLYZQYBAIRVLPF-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
- 239000002132 β-lactam antibiotic Substances 0.000 description 1
- 229940124586 β-lactam antibiotics Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/893,092 US4322347A (en) | 1978-04-03 | 1978-04-03 | 2-Carbamoyloxymethyl-penicillin derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE790947L IE790947L (en) | 1979-10-03 |
| IE49046B1 true IE49046B1 (en) | 1985-07-24 |
Family
ID=25401020
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE947/79A IE49046B1 (en) | 1978-04-03 | 1979-08-08 | Carbamoyloxy penicillin and cephalosporin derivatives and the production of 3-cephems |
Country Status (15)
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4374982A (en) * | 1979-11-07 | 1983-02-22 | Bristol-Myers Company | Cepham compounds |
| IT1148888B (it) * | 1980-07-15 | 1986-12-03 | Schiena Ricerche Di | Composti antibiotici |
| ZW13589A1 (en) * | 1988-10-31 | 1990-06-13 | Hoffmann La Roche | Panicillanic acid derivatives |
| US5604222A (en) * | 1993-12-27 | 1997-02-18 | Lupin Laboratories, Ltd. | Method for the preparation of 2-chloro sulfinyl azetidinones |
| US5578721A (en) * | 1994-07-11 | 1996-11-26 | Lupin Laboratories Limited | Process for preparation of 3-exomethylene cepham sulfoxide esters |
| RS56212B1 (sr) | 2011-12-20 | 2017-11-30 | Riboscience Llc | 2',4'-difluoro-2'-metilom supstituisani nukleozidni derivati kao inhibitori replikacije rna hcv-a |
| CN108409820A (zh) | 2011-12-20 | 2018-08-17 | 里博科学有限责任公司 | 作为hcv rna复制抑制剂的4′-叠氮基，3′-氟取代的核苷衍生物 |
| KR20160039154A (ko) | 2013-05-16 | 2016-04-08 | 리보사이언스 엘엘씨 | 4''-아자이도-3''-데옥시-3''-플루오로 치환된 뉴클레오시드 유도체 |
| MY186547A (en) | 2013-05-16 | 2021-07-26 | Riboscience Llc | 4?-fluoro-2?-methyl substituted nucleoside derivatives |
| US20180200280A1 (en) | 2013-05-16 | 2018-07-19 | Riboscience Llc | 4'-Fluoro-2'-Methyl Substituted Nucleoside Derivatives as Inhibitors of HCV RNA Replication |
| JP7299897B2 (ja) | 2017-09-21 | 2023-06-28 | リボサイエンス リミティド ライアビリティ カンパニー | Ｈｃｖのｒｎａ複製阻害剤としての４’－フルオロ－２’－メチル置換ヌクレオシド誘導体 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3275626A (en) * | 1962-07-31 | 1966-09-27 | Lilly Co Eli | Penicillin conversion via sulfoxide |
| US3714156A (en) * | 1970-06-22 | 1973-01-30 | Univ California | Lactam process |
| BE787618A (fr) | 1971-08-17 | 1973-02-16 | Gist Brocades Nv | Procede pour preparer des composes heterocycliques |
| GB1425827A (en) * | 1972-03-13 | 1976-02-18 | Astra Laekemedel Ab | Penicillins and cephalosporins |
| US4218374A (en) * | 1972-10-20 | 1980-08-19 | Fujisawa Pharmaceutical Company, Limited | Penam derivatives |
| GB1465893A (en) * | 1973-02-09 | 1977-03-02 | Gist Brocades Nv | I-carboxypropenyl-4-iminothio-azetidine-2-one derivatives methods for their preparation and use |
| DE2309599A1 (de) * | 1973-02-26 | 1974-09-05 | Bayer Ag | Verfahren zur herstellung von 7-acylamino-desacetoxy-cephalosporansaeurederivaten |
| DE2320040A1 (de) | 1973-04-19 | 1974-11-07 | Bayer Ag | Verfahren zur herstellung von 7acylamino-desacetoxy-cephalosporansaeureester |
| US4010156A (en) * | 1973-04-19 | 1977-03-01 | American Home Products Corporation | Process for the rearrangement of penicillins to cephalosporins and intermediate compounds thereof |
| GB1467604A (en) * | 1974-06-27 | 1977-03-16 | Toyama Chemical Co Ltd | Bis-type penicillins and process for producing the same |
| FR2340093A1 (fr) | 1976-02-05 | 1977-09-02 | Roussel Uclaf | Derives de l'acide 3-carbamoyloxymethyl 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments |
| GB1573614A (en) * | 1976-02-25 | 1980-08-28 | Leo Pharm Prod Ltd | Amidinopenicillanoyloxyalkyl cephalosporanates |
| DE2655949A1 (de) * | 1976-12-10 | 1978-06-15 | Gruenenthal Gmbh | Neue cephalosporin- und penicillinderivate, verfahren zu deren herstellung und diese produkte enthaltende arzneimittel |
| US4182711A (en) * | 1978-04-27 | 1980-01-08 | Bristol-Myers Company | Antibacterial agents of the β-lactam type |
| CA1125745A (en) * | 1978-11-20 | 1982-06-15 | Joseph Kaspi | PROCESS FOR PREPARING .beta.-LACTAM ANTIBIOTICS |
-
1978
- 1978-04-03 US US05/893,092 patent/US4322347A/en not_active Expired - Lifetime
-
1979
- 1979-02-26 CA CA000322307A patent/CA1140915A/en not_active Expired
- 1979-03-23 IT IT48457/79A patent/IT1116851B/it active
- 1979-03-29 FR FR7907972A patent/FR2421903B1/fr not_active Expired
- 1979-03-29 DK DK129779A patent/DK129779A/da unknown
- 1979-03-29 DE DE19792912483 patent/DE2912483A1/de not_active Withdrawn
- 1979-03-29 NL NL7902443A patent/NL7902443A/xx not_active Application Discontinuation
- 1979-03-30 BE BE0/194349A patent/BE875247A/xx not_active IP Right Cessation
- 1979-03-30 YU YU756/79A patent/YU41860B/xx unknown
- 1979-04-02 LU LU81108A patent/LU81108A1/de unknown
- 1979-04-02 SE SE7902916A patent/SE448239B/sv not_active IP Right Cessation
- 1979-04-03 JP JP3942679A patent/JPS54132594A/ja active Granted
- 1979-04-03 CH CH310279A patent/CH642080A5/fr not_active IP Right Cessation
- 1979-04-03 GB GB7911570A patent/GB2017705B/en not_active Expired
- 1979-08-08 IE IE947/79A patent/IE49046B1/en unknown
-
1982
- 1982-09-30 YU YU2204/82A patent/YU43096B/xx unknown
- 1982-09-30 YU YU2206/82A patent/YU42803B/xx unknown
- 1982-09-30 YU YU2205/82A patent/YU42802B/xx unknown
- 1982-09-30 YU YU2207/82A patent/YU42050B/xx unknown
-
1984
- 1984-04-13 SE SE8402089A patent/SE458609B/sv not_active IP Right Cessation
- 1984-04-13 SE SE8402090A patent/SE458610B/sv not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IE790947L (en) | 1979-10-03 |
| YU220682A (en) | 1983-01-21 |
| YU42803B (en) | 1988-12-31 |
| SE8402090L (sv) | 1984-04-13 |
| CH642080A5 (fr) | 1984-03-30 |
| YU75679A (en) | 1983-01-21 |
| BE875247A (fr) | 1979-10-01 |
| SE458610B (sv) | 1989-04-17 |
| US4322347A (en) | 1982-03-30 |
| YU43096B (en) | 1989-02-28 |
| NL7902443A (nl) | 1979-10-05 |
| SE8402089D0 (sv) | 1984-04-13 |
| YU220482A (en) | 1983-01-21 |
| GB2017705A (en) | 1979-10-10 |
| SE8402090D0 (sv) | 1984-04-13 |
| YU41860B (en) | 1988-02-29 |
| JPH0217557B2 (enrdf_load_stackoverflow) | 1990-04-20 |
| YU220782A (en) | 1983-01-21 |
| IT1116851B (it) | 1986-02-10 |
| DE2912483A1 (de) | 1979-10-11 |
| FR2421903A1 (fr) | 1979-11-02 |
| SE7902916L (sv) | 1979-10-04 |
| GB2017705B (en) | 1982-10-27 |
| IT7948457A0 (it) | 1979-03-23 |
| YU42050B (en) | 1988-04-30 |
| DK129779A (da) | 1979-10-04 |
| CA1140915A (en) | 1983-02-08 |
| YU42802B (en) | 1988-12-31 |
| SE458609B (sv) | 1989-04-17 |
| SE448239B (sv) | 1987-02-02 |
| FR2421903B1 (fr) | 1986-08-29 |
| LU81108A1 (de) | 1979-11-07 |
| SE8402089L (sv) | 1984-04-13 |
| YU220582A (en) | 1983-01-21 |
| JPS54132594A (en) | 1979-10-15 |
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